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MetaCyc Compound: IMP

Synonyms: 5'-IMP, ribosylhypoxanthine monophosphate, inosinate, inosine monophosphate, inosine 5'-monophosphate, inosine 5'-phosphate, 5'-inosinate, 5'-inosinic acid, 5'-inosine monophosphate

Superclasses: a nucleic acid component a nucleotide a nucleoside 5'-monophosphate a ribonucleoside 5'-monophosphate a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a ribonucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
a nucleic acid component a nucleotide a ribonucleotide a ribonucleoside 5'-monophosphate a purine ribonucleoside 5'-monophosphate
a nucleic acid component
an organic heterocyclic compound an organic heterobicyclic compound a purine a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate
an organic heterocyclic compound an organonitrogen heterocyclic compound a purine a purine nucleotide a purine ribonucleotide a purine ribonucleoside 5'-monophosphate

Chemical Formula: C10H11N4O8P

Molecular Weight: 346.19 Daltons

Monoisotopic Molecular Weight: 348.04709992489995 Daltons

IMP compound structure

SMILES: C(OP(=O)([O-])[O-])C1(OC(C(O)C(O)1)N3(C=NC2(C(=O)NC=NC=23)))

InChI: InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/p-2/t4-,6-,7-,10-/m1/s1

InChIKey: InChIKey=GRSZFWQUAKGDAV-KQYNXXCUSA-L

Unification Links: CAS:131-99-7 , ChEBI:58053 , ChemSpider:5482599 , HMDB:HMDB00175 , IAF1260:33960 , KEGG:C00130 , MetaboLights:MTBLC58053 , PubChem:7140378

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -244.30493 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

adenosine nucleotides degradation I :
IMP + H2O → inosine + phosphate

adenosine ribonucleotides de novo biosynthesis :
L-aspartate + IMP + GTP → adenylo-succinate + GDP + phosphate + 2 H+

Not in pathways:
IMP + H2O → hypoxanthine + D-ribofuranose 5-phosphate

Not in pathways:
a ribonucleoside 5'-monophosphate + H2O → a ribonucleoside + phosphate

Not in pathways:
ribonucleotiden + ribonucleotiden + ATP → ribonucleotidem+n + AMP + diphosphate

Not in pathways:
a nucleoside 5'-monophosphate[periplasmic space] + H2O[periplasmic space] → a nucleoside[periplasmic space] + phosphate[periplasmic space]
a nucleoside 5'-monophosphate + ATP → a nucleoside diphosphate + ADP

Not in pathways:
a nucleotide + H2O → a nucleoside + phosphate

Reactions known to produce the compound:

adenine and adenosine salvage V :
inosine + ATP → IMP + ADP + H+

adenosine nucleotides degradation I :
AMP + H+ + H2O → IMP + ammonium

Not in pathways:
IDP + H2O → IMP + phosphate + H+
ITP + H2O → IMP + diphosphate + H+
ammonium + IMP + NADP+ ← GMP + NADPH + 2 H+

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + H2O → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate
a tRNA precursor with a 5' extension and a short 3' extension → a tRNA precursor with a 5' extension + a ribonucleoside 5'-monophosphate

Not in pathways:
a single stranded DNA + H2O → a ribonucleoside 5'-monophosphate + a single-stranded oligodeoxyribonucleotide
a single-stranded RNA + n H2O → n a ribonucleoside 5'-monophosphate

Not in pathways:
a tRNA precursor + H2O → a tRNA + a ribonucleotide

tRNA processing :
a tRNA precursor with a 5' extension and a long 3' trailer + n H2O → a tRNA precursor with a 5' extension and a short 3' extension + n a nucleoside 5'-monophosphate
a tRNA precursor with a short 3' extension → an uncharged tRNA + n a nucleoside 5'-monophosphate

Not in pathways:
a nucleoside 3',5'-bisphosphate + H2O → a nucleoside 5'-monophosphate + phosphate
a nucleoside triphosphate + 2 H2O → a nucleoside 5'-monophosphate + 2 phosphate + 2 H+
a tRNA precursor + H2O → a tRNA + a nucleoside 5'-monophosphate
RNase II degradation substrate mRNA + n H2O → n a nucleoside 5'-monophosphate
mutated tRNA + n H2O → n a nucleoside 5'-monophosphate
DNAn + n H2O → n a nucleoside 5'-monophosphate
RNA + n H2O → n a nucleoside 5'-monophosphate
a double stranded DNA + H2O → a double stranded DNA + a nucleoside 5'-monophosphate
(deoxynucleotides)(n) + H2O → (deoxynucleotides)(n-1) + a nucleoside 5'-monophosphate
a RNA-DNA hybrid + n H2O → DNA + n a nucleoside 5'-monophosphate
a 2-O-methylated RNA + n H2O → n a nucleoside 5'-monophosphate
RNase R degradation substrate RNA + n-1 H2O → n-2 a nucleoside 5'-monophosphate + a diribonucleotide
an oligonucleotide + H2O → n a nucleoside 5'-monophosphate

Reactions known to both consume and produce the compound:

adenine and adenosine salvage III , adenine and adenosine salvage IV :
IMP + diphosphate ↔ hypoxanthine + 5-phospho-α-D-ribose 1-diphosphate

adenosine nucleotides degradation I , guanosine ribonucleotides de novo biosynthesis , urate biosynthesis/inosine 5'-phosphate degradation :
IMP + NAD+ + H2O ↔ XMP + NADH + H+

inosine-5'-phosphate biosynthesis I , inosine-5'-phosphate biosynthesis II , inosine-5'-phosphate biosynthesis III :
IMP + H2O ↔ 5-formamido-1-(5-phospho-D-ribosyl)-imidazole-4-carboxamide

In Reactions of unknown directionality:

Not in pathways:
a purine ribonucleoside + diphosphate = a purine ribonucleoside 5'-monophosphate + phosphate + H+

Not in pathways:
a nucleoside 5'-monophosphate + ATP = a 5'-phosphonucleoside 3'-diphosphate + AMP + H+
a lipopolysaccharide + a nucleoside diphosphocholine = a phosphorylcholine-6-O-hexose-lipopolysaccharide + a nucleoside 5'-monophosphate + H+
a dinucleotide (nucleic acid) + H2O = 2 a nucleoside 5'-monophosphate + 2 H+
a nucleoside diphosphate + H2O = a nucleoside 5'-monophosphate + phosphate + H+
a p-nitrophenyl 5'-nucleotide + H2O = a nucleoside 5'-monophosphate + 4-nitrophenol + 2 H+

Not in pathways:
a nucleotide + a 2'-deoxynucleoside = a nucleoside + a 2'-deoxyribonucleoside 5'-monophosphate

In Transport reactions:
IMP[cytosol]IMP[periplasmic space]

Enzymes activated by IMP, sorted by the type of activation, are:

Activator (Allosteric) of: carbamoyl phosphate synthetase [Anderson77, Trotta74]

Enzymes inhibited by IMP, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: phosphoribosylaminoimidazole-succinocarboxamide synthase [Nelson05]

Inhibitor (Mechanism unknown) of: amidophosphoribosyl transferase [Messenger79] , methylenetetrahydrofolate dehydrogenase [Dev78] , hypoxanthine phosphoribosyltransferase [Hochstadt78, Guddat02] , xanthine phosphoribosyltransferase [Liu83, Comment 1] , guanylate kinase [Oeschger66] , glycogen phosphorylase [Dombradi85]

This compound has been characterized as an alternative substrate of the following enzymes: alkaline phosphatase , farnesyl diphosphate phosphatase , guanylate kinase , AMP 5'-nucleotidase


References

Anderson77: Anderson PM (1977). "Binding of allosteric effectors to carbamyl-phosphate synthetase from Escherichia coli." Biochemistry 1977;16(4);587-93. PMID: 189806

Dev78: Dev IK, Harvey RJ (1978). "A complex of N5,N10-methylenetetrahydrofolate dehydrogenase and N5,N10-methenyltetrahydrofolate cyclohydrolase in Escherichia coli. Purification, subunit structure, and allosteric inhibition by N10-formyltetrahydrofolate." J Biol Chem 1978;253(12);4245-53. PMID: 350870

Dombradi85: Dombradi V, Hajdu J, Friedrich P, Bot G (1985). "Purification and characterization of glycogen phosphorylase from Drosophila melanogaster." Insect Biochem. Vol. 15, No. 3, pp. 403-410.

Guddat02: Guddat LW, Vos S, Martin JL, Keough DT, de Jersey J (2002). "Crystal structures of free, IMP-, and GMP-bound Escherichia coli hypoxanthine phosphoribosyltransferase." Protein Sci 11(7);1626-38. PMID: 12070315

Hochstadt78: Hochstadt J (1978). "Hypoxanthine phosphoribosyltransferase and guanine phosphoribosyltransferase from enteric bacteria." Methods Enzymol 1978;51;549-58. PMID: 692401

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Liu83: Liu SW, Milman G (1983). "Purification and characterization of Escherichia coli guanine-xanthine phosphoribosyltransferase produced by a high efficiency expression plasmid utilizing a lambda PL promoter and CI857 temperature-sensitive repressor." J Biol Chem 1983;258(12);7469-75. PMID: 6305942

Messenger79: Messenger LJ, Zalkin H (1979). "Glutamine phosphoribosylpyrophosphate amidotransferase from Escherichia coli. Purification and properties." J Biol Chem 1979;254(9);3382-92. PMID: 372191

Nelson05: Nelson SW, Binkowski DJ, Honzatko RB, Fromm HJ (2005). "Mechanism of action of Escherichia coli phosphoribosylaminoimidazolesuccinocarboxamide synthetase." Biochemistry 44(2);766-74. PMID: 15641804

Oeschger66: Oeschger MP, Bessman MJ (1966). "Purification and properties of guanylate kinase from Escherichia coli." J Biol Chem 1966;241(22);5452-60. PMID: 5333666

Trotta74: Trotta PP, Pinkus LM, Haschemeyer RH, Meister A (1974). "Reversible dissociation of the monomer of glutamine-dependent carbamyl phosphate synthetase into catalytically active heavy and light subunits." J Biol Chem 1974;249(2);492-9. PMID: 4358555


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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